Triethylamine → HCID 89874071, compound

HRID 715482Notes

Reaction equation

HRID 715482 reaction equation
Cl.[NH2:2][C:3]1[C:8]2[CH2:9][N:10]([CH:13]([C:15]3[CH:16]=[N:17][C:18]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[C:19]([CH3:21])[CH:20]=3)[CH3:14])[C:11](=[O:12])[C:7]=2[CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.[CH3:35][O:36][CH2:37][C:38](Cl)=[O:39]>C1COCC1.CCOC(C)=O>[CH3:35][O:36][CH2:37][C:38]([NH:2][C:3]1[C:8]2[CH2:9][N:10]([CH:13]([C:15]3[CH:16]=[N:17][C:18]([O:22][CH2:23][C:24]([F:26])([F:27])[F:25])=[C:19]([CH3:21])[CH:20]=3)[CH3:14])[C:11](=[O:12])[C:7]=2[CH:6]=[CH:5][N:4]=1)=[O:39]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 89875319HCID 89875319, compound

Product 1

HCID 89874071HCID 89874071, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-amino-2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one hydrochloride (20 mg, 0.050 mmol, Example-17, single enantiomer) and triethylamine (0.069 mL, 0.50 mmol) in THF (1.0 mL) is added 2-methoxyacetyl chloride (27 mg, 0.25 mmol) at rt. The reaction mixture is stirred for 21 hours at rt and diluted with EtOAc. The organic phase is washed with water and dried over sodium sulfate. After filtration, the filtrate and volatiles are removed. The residue is filtered through a short column of NH-gel eluting with EtOAc and the filtrate is concentrated in vacuo. The residue is purified by preparative LC-MS to give 8.5 mg (39% yield) of the title compound.

Workup

  1. washThe organic phase is washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationAfter filtration
  4. customthe filtrate and volatiles are removed
  5. filtrationThe residue is filtered through a short column of NH-gel
  6. washeluting with EtOAc
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified by preparative LC-MS

Sources & evidence

ORD record
ord-f74fe973ee894ef6ad950d0372ac3024
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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